Diethyl Ether → HCID 18335086, compound

HRID 2296827Notes

Reaction equation

HRID 2296827 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH2:18][OH:19])[CH:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].CI.[CH3:38]COCC>CS(C)=O>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH2:18][O:19][CH3:38])[CH:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[CH2:23][CH2:22]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 18723500HCID 18723500, compound

Product 1

HCID 18335086HCID 18335086, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.0025 g (0.057 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-hydroxymethylpyrrolidine, 0.013 g (0.23 mmol) of KOH and 0.028 mL (0.46 mmol) of methyl iodide in 2 mL of DMSO was stirred at rt for 1.2 h. The reaction mixture was poured into ether and washed with sat'd NaHCO3 and NaCl solutions, dried over Na2O4 and filtered. The filtrate was concentrated and the residue was purified by chromatography (silica, acetone: hexanes, 1:2) to give the compound.

Workup

  1. washwashed with sat'd NaHCO3 and NaCl solutions
  2. customdried over Na2O4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography (silica, acetone: hexanes, 1:2)
  6. customto give the compound

Sources & evidence

ORD record
ord-42d6af2cec4f4d7ca06a0872d75d4991
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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